


The Unlikely Bachelor

by My_wayward_CASsbutt



Category: Supernatural, destiel - Fandom
Genre: F/M, M/M, The Bachelorette - Freeform, destiel au, the bachelor - Freeform
Language: English
Status: In-Progress
Published: 2017-01-29
Updated: 2017-01-29
Packaged: 2018-09-20 18:27:40
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,795
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9505334
Author URL: https://archiveofourown.org/users/My_wayward_CASsbutt/pseuds/My_wayward_CASsbutt
Summary: As the result of a bet against his brother, Dean Winchester becomes a contestant on the reality TV show, The Bachelorette, where 30 men are in competition to win over the woman chosen for the season.   This season, the woman they're all meant to be pining for is the one and only Lisa Braeden. And Dean is 100% determined to hold up his end of the bet, charming her with his good looks and suave personality.But what happens when a shy, blue-eyed man also joins the competition in an attempt to convince his religious parents that he can indeed deny his homosexuality?I think we all know how this ends.





	

**Author's Note:**

> I completely despise everything that The Bachelorette is but I thought this was a cute prompt and I'm actually pretty excited about it :)
> 
> (So I suck and I posted the first chapter and then gave up but I swear I will continue it at some point soon. Stay tuned I am so sorry)

Introductions

“My name is Dean Winchester, I’m an aquarius and I like long walks on the beach.” The camera went to Dean driving down the road in his Impala. “My car is my life and the only family I have is my brother. “ We then see Dean sitting on the couch next to a tall man with hair too long for his own good, “I’m a mechanic in Lawrence, Kansas, and I’m just looking for a lady to fill that empty side of my bed.” Back to Dean’s face, he winked, “And uh, you’ll just have to watch to know the rest.”

The interviews went through about 18 more people until landing on a very nervous man with raven hair. 

“I don’t understand, why do you want me to say my name?” Beep “Oh, hello, my name is Castiel James Novak. I’m 38 years old and I live in Pontiac, Illinois. Is that it?” Beep “Ok, ummmm, my family is very religious,” camera cuts to him sitting on a bench outside a church, “my father is actually a pastor and my mother conducts a bible study group every weekend.” Now we see him sitting with a group of people, all holding copies of the bible, “She loves the show, she’s actually the reason I’m here,” We cut back to his face, “this was her idea, she says I just haven’t met ‘the one’ yet. I guess you could say my ‘people skills’ are a little ‘rusty’. Ok, uh that’s all.”

There were about 11 more interviews after Castiel Novak but those aren’t important so let’s just get right into it.

 

DEANS POV

I had readjusted my suit a zillion times already, but I did it again hoping that maybe this time my damn pants wouldn’t squeeze me in all the wrong places. I had to admit I did look pretty sexy though.

“Guys, I’m so psyched!!” Bartholomew said form the other side of the limo, “I still can’t believe Lisa Braeden is the Bachelorette!! She’s so hot!” 

“Damn right!” Balthazar added, giving Bartholomew a high-five.

“Yeah she’s real cute, ain’t she?” Garth joined the conversation. 

I had just met all these guys when we first got into the limo, but we all seemed to be bonding well. We’d just been lightly drinking and putting up with as much small talk as we could stand. Where we worked, why we were here, our families, past relationships. The works.

Everyone began talking about all Lisa’s great qualities, while I sat on the sidelines, observing the men I was about to jump into the ring with. I had to come into this with my best foot forward, preferably the best foot America had ever seen. Now I’m not gonna pretend that this isn’t the lamest reality tv show in the history of reality tv shows, but it came on one night after an episode of Doctor Sexy M.D. and the encounter went a little like this:

Sam: *walks in* Are you watching The Bachelorette??

Me: ahem, No, I was uh, watching the football game and my remote wacked out. It happens.

Sam: sure…

Me: Sam. No.... 

Sam: Hm, You looked pretty intrigued when I walked i n just now.

Me: Shut up, I was not..... Plus the only people on this show are pretty boys who would rather cry over a plate of roses, and broadcast their relationship in People magazine than actually go out and meet a girl in the real world like the rest of us.

Sam: Hm. Pansies huh? I bet you 100 bucks you couldn’t do it. 

Me: What?

Sam: Yeah. You’re probably just bashing them ‘cause you’re too scared to do it yourself.

Me: Am not!!

Sam: Really?

Me: Really.

Sam: Do it then.

Me: …Sam

Sam: Dean.

Me: Absolutely not.

Sam: I was right then

Me: Fine! I’ll do it! But remember you said 100 bucks. 

Sam: Yeah? You’ll do it?

Me: ...Ugh…

So we shook on it and next thing I knew Sam had his laptop out and we were signing me up for the next season of The Bachelorette. I still hated the idea but I’d be damned if I wasn’t gonna hold up my end of the bet, regardless of how ridiculous it was. I was a man of my word, and I wasn’t gonna disappoint now.

I decided I would go into this quietly, maybe with a bit of mystery, leave them wanting more. While these guys were all waving their dicks in the air, I would be charming the Bachelorette with my good looks and suave personality

I was gonna come away from this with a reputation, $100, and if I played my cards right, a wife.

 

The limo stopped in front of a huge house/mansion/castle thing, and since I was the closest to the door I was gonna be the first to introduce myself. Lisa was standing in a long, sleeveless, green dress, that she filled out nicely in the chest area. Needless to say I was excited. 

I stepped out of the limo and made my way towards her. She smiled and I smiled back, then we hugged, and I don’t really remember anything after that. All I know is that it was awkward, like every bachelor/bachelorette meeting is. Don’t ask me how I know that.

I told her to come find me inside when she was done meeting everyone else. Then I smirked and made my way into the sitting area of the house. 

The other guys from the limo began filing in. All of them were still as excited as I had seen them before, it kinda felt like a formal frat party. I looked to my left and saw a window that gave a clear view of Lisa and whoever she was talking to. I watched her say hello to about ten guys until she made it to one who specifically stood out, probably because of how nervous he was. I didn’t recognize him from my limo, he was probably in the next one. Jeez the introductions are going by fast. They hugged and said hello and I could tell Lisa noticed his nervousness too. Great minds think alike. She put her hand on his shoulder and gave him a reassuring smile. They talked for about 15 seconds until she sent him inside. 

When he walked in a few guys stood and shook his hand, others said hello, and handed him a drink. I couldn’t help but notice how messy his hair was, but somehow he made it work. He sat in between a young guy who had introduced himself as Adam and that asshole from my limo, Bartholomew. He didn’t speak unless he was spoken to and overall just looked really uncomfortable. 

I looked back out the window and watched Lisa a little longer, she was still greeting guys. They were going by really fast but it was still too long. I selfishly wanted her to be done so I could have a chance to talk to her. I took a sip of my drink and went over what I was gonna say to her. I heard from Sam, who watches all the seasons - Fangirl much?- that she had a kid. Billie? Ben? Brock? I don’t know, one of those. Maybe I could start with something about how good I was with kids.

I suddenly felt like I was being watched and looked ahead of me. That guy from before was watching me. I couldn’t help but notice he had really blue eyes. Damn. Once he saw that I had caught him staring he turned his attention to his untouched drink. He then brought it up to his mouth and chugged the whole thing. Jeez. This was probably gonna be a very long night for him. I wonder what his deal is? Is he like this uber introvert? Has he ever talked to a women before? Has he ever talked to anyone before?

He wiped the side of his mouth and Bartholomew slapped him on the back and cheered. I looked once again out the window but Lisa wasn’t there. 

“Alright boys, thank you all for coming.” she was standing right in front of us, “I’m gonna try and get to all of you tonight, so let’s just keep it simple and keep it fair, alright?”

Everyone nodded and Bartholomew stood asking if he could be the first to speak with her. Asshole. She smiled and they walked outside to the area by the pool. I could see them through another window to my right. I reevaluated my game plan and decided that if I wanted to talk to her tonight I was gonna have to play dirty. This was obviously a game of taking what you wanted when you wanted it, not politely waiting around for it to be handed to you. Some guy by the name of Uriel stood and walked out the door that they exited through. I took a swig of my beer, and watched a s he interrupted Lisa’s conversation with Bartholomew. There are 30 guys here, how is this going to work? 

I heard some of the guys laughing (harder than usual), and I turned to see what the fuss was about. They were all sat around a blond man with a pretty confident look on his face. He gave me a weird vibe so I decided to steer clear of him. 

“What are you looking at?” he said to me. I made an act of pointing to my chest like I didn’t know who he was talking to, “Yes, you.”

“Just observing the competition”

“Oh yeah? You think that you’ve got a chance against me?”

I sat up taller and took a swig of my beer, “I mean, isn’t that why we’re all here?”

He considered this, and with a turned up chin and a cocky attitude he said, “I suppose you have point. And what’s your name big guy?”

“Winchester. Dean Winchester.” I’d always wanted to do that.

“Well Dean Winchester, I’m Lucifer.” We shook hands. “May the best man win.”

“Now now, Lucifer, I think we ought-a at least humour the rest of these guys a little bit, wouldn’t you agree.”

“You’re probably right. Can’t pose as a threat too early in the game, we might not make any friends that way. You gotta start off with a little cat and mouse if you will. He leaned in a bit closer, I don’t know why, but I have a feeling you and I are gonna be the last one’s standing at the end of this.”

“I think you might be right. The only question is, where will it go from there” I smirked. So much for steering clear.


End file.
